Airbnb Properties for Sale in Oakland, FL

Looking for a vacation rental investment in Oakland, FL with high ROI ?

Explore a range of newly added short-term rental homes in Oakland, FL. Make a smart investment with newly available Airbnb properties and find the ideal high-ROI property for sale.

Airbnb For Sale in Oakland, FL

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PROPERTY	DETAILS	SALE PRICE	INVESTMENT PERFORMANCE
250 N Walker St Oakland, FL 250 N Walker St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 2,469 sq.ft.	$1,295,000	Airbnb cash on cash: 1.39% Traditional cash on cash: 0.12% Airbnb Rental Income: $5064 Traditional Rental Income: $2504 Airbnb ROI: 1.39% Traditional ROI: 0.12%
38 S Pollard St Oakland, FL 38 S Pollard St, Oakland, FL 34760 \| Single Family Residential	4 beds \| 2 baths \| 1,872 sq.ft.	$699,000	Airbnb cash on cash: 4.16% Traditional cash on cash: 1.78% Airbnb Rental Income: $5064 Traditional Rental Income: $2480 Airbnb ROI: 4.16% Traditional ROI: 1.78%
310 E GULLEY AVENUE Oakland, FL Under contract-accepting backup offers. Beautifully renovated pool home in the desirable T...	3 beds \| 2 baths \| 1,763 sq.ft.	$695,000	Airbnb cash on cash: 3.38% Traditional cash on cash: 3.18% Airbnb Rental Income: $3912 Traditional Rental Income: $2944 Airbnb ROI: 3.38% Traditional ROI: 3.18%
2259 White Feather Loop Oakland, FL ABSOLUTELY STUNNING 4/2.5 PLUS LOFT HOME LOCATED ON A CORNER LOT IN OAKLAND TRAILS. UPON E...	4 beds \| 2 baths \| 2,204 sq.ft.	$525,000	Airbnb cash on cash: 6% Traditional cash on cash: 2.68% Airbnb Rental Income: $5064 Traditional Rental Income: $2402 Airbnb ROI: 6% Traditional ROI: 2.68%
729 Strihal Loop Oakland, FL One or more photo(s) has been virtually staged. Once-in-a-Lifetime Opportunity! *EXTERIO...	4 beds \| 3 baths \| 3,583 sq.ft.	$679,900	Airbnb cash on cash: 4.41% Traditional cash on cash: 4.36% Airbnb Rental Income: $5064 Traditional Rental Income: $4002 Airbnb ROI: 4.41% Traditional ROI: 4.36%
2120 GOPHER TORTOISE TERRACE Oakland, FL Welcome to 2120 Gopher Tortoise Terrace in charming Oakland, Florida, a beautifully mainta...	3 beds \| 3 baths \| 1,620 sq.ft.	$379,900	Airbnb cash on cash: 4.98% Traditional cash on cash: 3.81% Airbnb Rental Income: $3912 Traditional Rental Income: $2653 Airbnb ROI: 4.98% Traditional ROI: 3.81%
2065 White Feather Loop Oakland, FL Welcome to the highly desirable Oakland Trails community, where this exceptional 2019 Meri...	3 beds \| 2 baths \| 2,089 sq.ft.	$549,900	Airbnb cash on cash: 3.58% Traditional cash on cash: 3.21% Airbnb Rental Income: $3912 Traditional Rental Income: $2879 Airbnb ROI: 3.58% Traditional ROI: 3.21%
624 Hull Island Dr Oakland, FL 624 Hull Island Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,708 sq.ft.	$894,000	Airbnb cash on cash: 2.85% Traditional cash on cash: 2.04% Airbnb Rental Income: $5064 Traditional Rental Income: $3361 Airbnb ROI: 2.85% Traditional ROI: 2.04%
1270 Stationside Drive Dr Oakland, FL 1270 Stationside Drive Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 2 baths \| 2,046 sq.ft.	$519,000	Airbnb cash on cash: 6.17% Traditional cash on cash: 2.24% Airbnb Rental Income: $5064 Traditional Rental Income: $2126 Airbnb ROI: 6.17% Traditional ROI: 2.24%
1156 CIVITAS WAY Oakland, FL Welcome to this exceptional 2022 RCB custom home in Oakland Park, one of Central Florida's...	4 beds \| 3 baths \| 2,710 sq.ft.	$1,275,000	Airbnb cash on cash: 1.25% Traditional cash on cash: 0.68% Airbnb Rental Income: $5064 Traditional Rental Income: $3349 Airbnb ROI: 1.25% Traditional ROI: 0.68%
2228 Gopher Tortoise Ter Oakland, FL 2228 Gopher Tortoise Ter, Oakland, FL 34787 \| Townhouse	3 beds \| 2 baths \| 1,620 sq.ft.	$395,000	Airbnb cash on cash: 4.88% Traditional cash on cash: 1.97% Airbnb Rental Income: $3912 Traditional Rental Income: $1994 Airbnb ROI: 4.88% Traditional ROI: 1.97%
2222 GOPHER TORTOISE TERRACE Oakland, FL YOU Must see this absolutely Gorgeous 3BEDS,3 FULL BATH Townhouse in Oakland. located Betw...	3 beds \| 3 baths \| 1,809 sq.ft.	$416,900	Airbnb cash on cash: 4.13% Traditional cash on cash: 3.51% Airbnb Rental Income: $3912 Traditional Rental Income: $2831 Airbnb ROI: 4.13% Traditional ROI: 3.51%
1412 Johns Cove Ln Oakland, FL 1412 Johns Cove Ln, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,613 sq.ft.	$1,499,000	Airbnb cash on cash: 0.81% Traditional cash on cash: 0.48% Airbnb Rental Income: $5064 Traditional Rental Income: $3584 Airbnb ROI: 0.81% Traditional ROI: 0.48%
8 Winters Landing Dr Oakland, FL 8 Winters Landing Dr, Oakland, FL 34787 \| Single Family Residential	4 beds \| 3 baths \| 2,850 sq.ft.	$885,000	Airbnb cash on cash: 2.8% Traditional cash on cash: 1.05% Airbnb Rental Income: $5064 Traditional Rental Income: $2592 Airbnb ROI: 2.8% Traditional ROI: 1.05%
1231 Foltz Loop Oakland, FL 1231 Foltz Loop, Oakland, FL 34787 \| Single Family Residential	4 beds \| 4 baths \| 3,134 sq.ft.	$874,900	Airbnb cash on cash: 2.72% Traditional cash on cash: 1.5% Airbnb Rental Income: $5064 Traditional Rental Income: $3036 Airbnb ROI: 2.72% Traditional ROI: 1.5%
2117 Gopher Tortoise Ter Oakland, FL 2117 Gopher Tortoise Ter, Oakland, FL 34787 \| Townhouse	2 beds \| 2 baths \| 1,472 sq.ft.	$364,900	Airbnb cash on cash: 3.64% Traditional cash on cash: 2.11% Airbnb Rental Income: $3176 Traditional Rental Income: $1936 Airbnb ROI: 3.64% Traditional ROI: 2.11%
2135 STANDING ROCK CIRCLE Oakland, FL Under contract-accepting backup offers. ASSUMABLE 2.4% Interest Rate. Welcome to this b...	3 beds \| 3 baths \| 2,078 sq.ft.	$474,990	Airbnb cash on cash: 4.45% Traditional cash on cash: 4.03% Airbnb Rental Income: $3912 Traditional Rental Income: $2887 Airbnb ROI: 4.45% Traditional ROI: 4.03%
2660 BOBCAT CHASE BOULEVARD Oakland, FL Under contract-accepting backup offers. Welcome to your peaceful retreat in the heart of O...	3 beds \| 3 baths \| 1,811 sq.ft.	$525,000	Airbnb cash on cash: 3.49% Traditional cash on cash: 3% Airbnb Rental Income: $3912 Traditional Rental Income: $2834 Airbnb ROI: 3.49% Traditional ROI: 3%

Vacation Rentals in Oakland

There are 18 vacation rental properties available for sale in the city of Oakland . The median list price of Airbnb properties available for sale in Oakland is $679,900 and the average price per square foot is $368. The cash on cash return on vacation rentals in Oakland is 3.00%. The average monthly short term rental income in Oakland is $3,912.

Oakland, FL Short Term Rentals FAQs for Buyers, Sellers and Investors

There are 18 Airbnb properties available for sale in Oakland.

In 2026, the best neighborhood to buy short term rental property is Oakland.

In April 2026, the average Airbnb occupancy rate in Oakland is 72%.

Airbnb data on vacation rentals in Oakland, FL is available at Mashvisor. You can access data such as listings, real-time pricing trends, Oakland, FL market insights, guest information and booking details, seasonality trends and historical Oakland, FL Airbnb performance data.

Your search for investment property begins and ends here

Airbnb For Sale in Oakland, FL

250 N Walker St

Oakland, FL

4 beds | 2 baths | 2,469 sq.ft.

$1,295,000

Airbnb cash on cash: 1.39%

Traditional cash on cash: 0.12%

Airbnb Rental Income: $5064

Traditional Rental Income: $2504

Airbnb ROI: 1.39%

Traditional ROI: 0.12%

38 S Pollard St

Oakland, FL

4 beds | 2 baths | 1,872 sq.ft.

$699,000

Airbnb cash on cash: 4.16%

Traditional cash on cash: 1.78%

Airbnb Rental Income: $5064

Traditional Rental Income: $2480

Airbnb ROI: 4.16%

Traditional ROI: 1.78%

310 E GULLEY AVENUE

Oakland, FL

3 beds | 2 baths | 1,763 sq.ft.

$695,000

Airbnb cash on cash: 3.38%

Traditional cash on cash: 3.18%

Airbnb Rental Income: $3912

Traditional Rental Income: $2944

Airbnb ROI: 3.38%

Traditional ROI: 3.18%

2259 White Feather Loop

Oakland, FL

4 beds | 2 baths | 2,204 sq.ft.

$525,000

Airbnb cash on cash: 6%

Traditional cash on cash: 2.68%

Airbnb Rental Income: $5064

Traditional Rental Income: $2402

Airbnb ROI: 6%

Traditional ROI: 2.68%

729 Strihal Loop

Oakland, FL

4 beds | 3 baths | 3,583 sq.ft.

$679,900

Airbnb cash on cash: 4.41%

Traditional cash on cash: 4.36%

Airbnb Rental Income: $5064

Traditional Rental Income: $4002

Airbnb ROI: 4.41%

Traditional ROI: 4.36%

2120 GOPHER TORTOISE TERRACE

Oakland, FL

3 beds | 3 baths | 1,620 sq.ft.

$379,900

Airbnb cash on cash: 4.98%

Traditional cash on cash: 3.81%

Airbnb Rental Income: $3912

Traditional Rental Income: $2653

Airbnb ROI: 4.98%

Traditional ROI: 3.81%

2065 White Feather Loop

Oakland, FL

3 beds | 2 baths | 2,089 sq.ft.

$549,900

Airbnb cash on cash: 3.58%

Traditional cash on cash: 3.21%

Airbnb Rental Income: $3912

Traditional Rental Income: $2879

Airbnb ROI: 3.58%

Traditional ROI: 3.21%

624 Hull Island Dr

Oakland, FL

4 beds | 2 baths | 2,708 sq.ft.

$894,000

Airbnb cash on cash: 2.85%

Traditional cash on cash: 2.04%

Airbnb Rental Income: $5064

Traditional Rental Income: $3361

Airbnb ROI: 2.85%